(4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-10-[(2S,3R,4R,5R)-5-[(2R,3R,4S,5R,6S)-3,4-dihydroxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxyoxan-2-yl]oxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid

Details

• Internal ID: c8ee9387-065b-4543-bf25-cd1f0f063859
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-10-[(2S,3R,4R,5R)-5-[(2R,3R,4S,5R,6S)-3,4-dihydroxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxyoxan-2-yl]oxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• SMILES (Canonical): CC1C(C(C(C(O1)OC2COC(C(C2O)O)OC3CCC4(C(C3(C)CO)CCC5(C4CC=C6C5(CCC7(C6CC(CC7)(C)C)C(=O)O)C)C)C)O)O)OC8C(C(C(C(O8)COC9C(C(C(C(O9)CO)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)O[C@@H]2CO[C@H]([C@@H]([C@H]2O)O)O[C@H]3CC[C@]4([C@H]([C@]3(C)CO)CC[C@@]5([C@@H]4CC=C6[C@]5(CC[C@@]7([C@H]6CC(CC7)(C)C)C(=O)O)C)C)C)O)O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O)O)O)O
• InChI: InChI=1S/C53H86O22/c1-23-42(75-46-40(64)36(60)33(57)27(73-46)20-68-43-39(63)35(59)32(56)26(19-54)71-43)37(61)41(65)45(70-23)72-28-21-69-44(38(62)34(28)58)74-31-11-12-49(4)29(50(31,5)22-55)10-13-52(7)30(49)9-8-24-25-18-48(2,3)14-16-53(25,47(66)67)17-15-51(24,52)6/h8,23,25-46,54-65H,9-22H2,1-7H3,(H,66,67)/t23-,25-,26+,27+,28+,29+,30+,31-,32+,33+,34-,35-,36-,37-,38+,39+,40+,41+,42-,43+,44-,45+,46-,49-,50-,51+,52+,53-/m0/s1
• InChI Key: MQDPNHFRYVCDQE-XIBDXIPFSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₃H₈₆O₂₂
• Molecular Weight: 1075.20 g/mol
• Exact Mass: 1074.56107437 g/mol
• Topological Polar Surface Area (TPSA): 354.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): -0.83
• H-Bond Acceptor: 21
• H-Bond Donor: 13
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7499	74.99%
Caco-2	-	0.8772	87.72%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.8758	87.58%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8287	82.87%
OATP1B3 inhibitior	-	0.5977	59.77%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5776	57.76%
BSEP inhibitior	+	0.9049	90.49%
P-glycoprotein inhibitior	+	0.7446	74.46%
P-glycoprotein substrate	-	0.5232	52.32%
CYP3A4 substrate	+	0.7345	73.45%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8798	87.98%
CYP3A4 inhibition	-	0.9589	95.89%
CYP2C9 inhibition	-	0.8763	87.63%
CYP2C19 inhibition	-	0.9003	90.03%
CYP2D6 inhibition	-	0.9427	94.27%
CYP1A2 inhibition	-	0.8671	86.71%
CYP2C8 inhibition	+	0.7477	74.77%
CYP inhibitory promiscuity	-	0.9423	94.23%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6313	63.13%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.9020	90.20%
Skin irritation	-	0.6520	65.20%
Skin corrosion	-	0.9500	95.00%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8251	82.51%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.8125	81.25%
skin sensitisation	-	0.8940	89.40%
Respiratory toxicity	-	0.6778	67.78%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	-	0.7750	77.50%
Nephrotoxicity	-	0.6620	66.20%
Acute Oral Toxicity (c)	III	0.7822	78.22%
Estrogen receptor binding	+	0.8266	82.66%
Androgen receptor binding	+	0.7375	73.75%
Thyroid receptor binding	+	0.5539	55.39%
Glucocorticoid receptor binding	+	0.7479	74.79%
Aromatase binding	+	0.6645	66.45%
PPAR gamma	+	0.8163	81.63%
Honey bee toxicity	-	0.6717	67.17%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5750	57.50%
Fish aquatic toxicity	+	0.9603	96.03%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.16%	91.11%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	96.52%	95.17%
CHEMBL3714130	P46095	G-protein coupled receptor 6	94.34%	97.36%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.26%	97.09%
CHEMBL221	P23219	Cyclooxygenase-1	91.56%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.68%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.97%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.48%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.26%	95.56%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	86.07%	95.50%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.22%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.21%	96.77%
CHEMBL5028	O14672	ADAM10	83.90%	97.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.81%	99.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.41%	99.23%
CHEMBL2581	P07339	Cathepsin D	81.88%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.41%	95.89%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.03%	96.90%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.69%	100.00%

Plants that contains it

• Cephalaria transsylvanica

Cross-Links

• PubChem: 162997614
• LOTUS: LTS0103377
• wikiData: Q105169923